1 - 20 of 115 Bookmarks by Pittleberry
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You and your dearest friend, John Carter, have a special way of blowing off steam at work.
Bookmarked by Pittleberry
17 Oct 2026
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Dennis went back into the living room and picked up the box from the coffee table. He stared at it intently, like he might be able to see through the cardboard if he only looked hard enough. There was no way Robby had just sent him a vibrator. Unable to simply stare at it any longer, he ripped the box open, took a deep breath, and looked inside.
In a way, he was right, Robby had not just sent him a vibrator. He'd sent him lube, toy cleaner, and something called a Connect App Liquid Air Technology Double Air Pulse Vibrator.
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Kinktober Day 12: Phone Sex
- Language:
- English
- Words:
- 2,731
- Chapters:
- 1/1
- Collections:
- 1
- Comments:
- 5
- Kudos:
- 229
- Bookmarks:
- 11
- Hits:
- 1,380
Bookmarked by Pittleberry
17 Oct 2026
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Whitaker is knocked out, stretched out in the middle of his bed with the duvet kicked all the way to his knees. It's a pretty sight, even though his wide-open mouth is releasing apneic snores and a sheen of drool is surrounding his lips.
Robby stands there for far too long, counting the moles spattered down his torso. They resemble a starry sky, and he wonders why he even left, when the best view he's seen in the last three months is right in his bedroom.
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Five times Robby finds Dennis sleeping + one time they fall asleep together.
Bookmarked by Pittleberry
13 Oct 2026
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The plants were still alive. Whitaker considered this a personal achievement. One of them had developed a new leaf. Whitaker crouched beside it.
“Well, look at you.”
He looked around. There was something almost absurd about how comfortable he had become. A few days ago, he had been afraid of breaking a vase, now there were groceries in Robby’s refrigerator.
And somewhere, unnoticed by him, a tiny camera quietly watched.
Bookmarked by Pittleberry
12 Oct 2026
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Robby craved to have that wet heat squeezing him, milking his cock for all he's worth and see the cum slowly drip out of Dennis. He wants to listen to the younger man whimper when Robby shoves it back in with his fingers.
Anything to make sure it takes.
Anything to make sure he stays.
or
kinktober day one - condoms
Bookmarked by Pittleberry
12 Oct 2026
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Dennis is fine.
He’s happy.
It’s all chill.
Except for one teeny tiny problem.
Aka, his massive, all consuming crush on his boss.
It’s… it’s a thing. It’s also a problem. It’s just… fuck. It’s just kind of awful. Dennis personally likes to think that it’s not his fault, because how the fuck else is he supposed to react to the hottest man he’s ever laid eyes on constantly grabbing and manhandling him and treating him like his personal project? Literally what is he supposed to do except fall head over heels for him?
Series
- Part 4 of tumblr pitt prompts!
- Part 2 of make a fool of my heart
Bookmarked by Pittleberry
12 Oct 2026
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The day Dr. Jack Abbot accidentally calls you "baby" on a shift is the day that everything changes.
Bookmarked by Pittleberry
05 Oct 2026
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After a case involving kink culture, Spencer is assigned to judge the girls’ game of Never Have I Ever. Later, him and Reader compare scores.
Bookmarked by Pittleberry
04 Oct 2026
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“So. You like baseball?”
Even now, the fact that those were the next words out of Robby’s mouth is almost unbelievable to him. Until this summer, Dennis doesn’t think he’d been asked that question his entire life and now, it’s come up twice—first, on the day Robby left, and now again on the day of Robby’s return. It struck him as some strange kismet, sort of like an incomplete thought finally circling back around. The answer, without question, was and is an easy no. Even if you didn’t factor a rural Nebraskan upbringing into the equation, for most of his life, he wasn’t exactly encouraged in that direction. Dennis, however, had a sense that he understood where Doctor Robby was going, and wanted very much for him to continue. Robby, therefore, did not receive the spiel about the Omaha Storm Chasers that Roberto with the dislocated elbow received on the Fourth of July. Instead, Dennis smiled and shrugged. “Sure, who doesn’t.”
“America’s pastime,” said Robby, pleased.
—
Robby takes Dennis out.
Bookmarked by Pittleberry
29 Sep 2026
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Dennis made a very unfortunate decision to confess to his boss, who is twice his age, and now things are awkward because he was rejected.
Bookmarked by Pittleberry
26 Sep 2026
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“...was just thinking about how your hips would feel fucking me.”
Dennis breathed in sharply. Which wasn't a great choice as he was still under the showerhead and promptly took in a mouthful of water.
“Told you.”
It took him a moment to recover, sputtering and spitting water before going quiet. When Robby finally opened his eyes again, Dennis was staring back at him with a soft expression that he couldn't quite read.
“You’re drunk.” He says it like Robby just told him a joke.
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Transpittweek day 2 "Teach me"- Language:
- English
- Words:
- 20,478
- Chapters:
- 1/1
- Collections:
- 1
- Comments:
- 67
- Kudos:
- 704
- Bookmarks:
- 174
- Hits:
- 8,593
Bookmarked by Pittleberry
25 Sep 2026
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Whilst housesitting, Dennis accidentally stumbles across something Robby forgot about a long time ago, and has three months to get acquainted with it. OR the fic where Dennis finds a silicone cast of Robby's dick and finds it too comforting to swear off.
Bookmarked by Pittleberry
23 Sep 2026
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Sure, Robby had a reputation for being a bit of a flirt, but he also had boundaries. She assumed (hoped?) that those boundaries excluded wide-eyed, twenty-something year old med students.
OR
5 times the PTMC staff were worried about Robby's inappropriate behavior towards Whitaker + 1 time they realized Whitaker was exactly where he wanted to be.
- Language:
- English
- Words:
- 13,158
- Chapters:
- 6/6
- Comments:
- 118
- Kudos:
- 1,219
- Bookmarks:
- 212
- Hits:
- 15,402
Bookmarked by Pittleberry
23 Sep 2026
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Trinity claims the walls are thin in their apartment, and his mattress creaks too loudly. So he quits jerking off when she's home. Struggling to find a moment of private, Dr. Robby catches him in the act, and finds he's not unaffected by the situation.
Bookmarked by Pittleberry
23 Sep 2026
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Dennis Whitaker’s shoes fall apart. Trinity headbutts a break-up in the face. Robby starts conversation.
Bookmarked by Pittleberry
22 Sep 2026
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It’s their first Valentine’s Day together and Robby thinks he’s being romantic by cooking a meal. Dennis takes a different approach.
Series
- Part 4 of I love da pitt
Bookmarked by Pittleberry
20 Sep 2026
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After Whitaker helps him through his panic attack, Robby doesn't feel like he's thanked the boy enough for all his help. After watching him and noticing things, he thinks of the perfect way to show Whitaker just how thankful he is...
Bookmarked by Pittleberry
19 Sep 2026
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On a porch, in the dark, somewhere in Broken Bow, Nebraska, on a random autumn Saturday, Robby brings his cigarette to Dennis' lips, as if it is the easiest thing in the world. But there is so much more to this one act of kindness, in the way his fingers brush against Dennis' lips, the way Dennis looks up at him through his lashes, eyes wide on his parents' porch. Dennis fears he might lose the family that raised him, but he isn't as scared, if it means he might gain a new one.
After Dennis' parents find out that he is trans and has been transitioning ever since leaving for medical school, Dr. Robby offers to drive him home to his parents, to do damage control.
- Language:
- English
- Words:
- 48,540
- Chapters:
- 5/5
- Comments:
- 314
- Kudos:
- 1,870
- Bookmarks:
- 436
- Hits:
- 29,459
Bookmarked by Pittleberry
18 Sep 2026
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The arrangement had been something they agreed upon at the start of their relationship, almost as soon as things became official.
In the safety of their home, they could take what they needed from the other whenever they needed it. Should one of them truly not want it to happen, their safe word was always there, ready to be deployed if needed.
OR
Dennis and Robby have a mutual free use agreement!
Bookmarked by Pittleberry
16 Sep 2026
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Summary
“Whitaker, are you in h—oh.”
Dennis turns to see Robby in the doorway, his eyes round and surprised, gaze not meeting Dennis’s, but instead fixed lower on—
He looks at his body, following the trail of Robby’s gaze down the sloping lines of his top to the wide strip of his exposed midriff. Skin on display, pale and scattered with a few small moles and a light patch of hair that dips down below the scalloped edge of baby blue lace that peeks up over the waistband of his scrubs.
Fuck. Shit. Fuckshitfuck.
OR: Dennis likes pretty things and Robby sees him in them on accident.
Bookmarked by Pittleberry
16 Sep 2026